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Chopped challenge #5: Tiramisu Trifles

When I quizzed her about this set of ingredients, my mom (it’s her birthday today; happy birthday, Mommy!) immediately said cheesecake, and as I think about it, that makes a lot of sense. The wafers and espresso get pulverized into a caffeinated crust, the balsamic becomes some sort of glaze or syrup for drizzling, and the cream cheese is allow to stay pristine and tangy in the center.

But as soon as I heard the espresso powder component of this quartet, my mind went to tiramisu, that famous Italian dessert of soaked ladyfingers piled with rich custard. The best tiramisu I’ve ever had was in a lovely little restaurant in Ashland, Oregon, now sadly defunct. Our server, overwhelmed by the busyness of the evening, brought us a free slice in an effort, I’ve always thought, to get us to stay a little longer so she wouldn’t immediately be hit with another new table of guests. It was so good – the custard silky and thick, the cookies melting after their marsala and coffee bath, and just the right dusting of completely unsweetened cocoa powder across the top to contrast the sweetness of the dessert and enhance the coffee flavors.

Mine would obviously be a little different. The chocolate wafers, in all their Styrofoam-textured glory, would clearly take the place of the ladyfingers (confession: I love these terrible cookies. I love their waffled surface design and their overly sweet filling and their fake, near tasteless exteriors. We had to hide the package while I planned this recipe out because I was going through them at least two at a time every time I walked past them). They would be soaked in espresso, and the cream cheese would be folded into the custard as a replacement for some of the traditional mascarpone.

The sticking point was the balsamic vinegar. After some consideration, I determined I would add some to the espresso to soak the cookies (and spent an entertaining few minutes tasting the wafers with some vinegar dribbled on and deeming them “weird but not terrible” – this is what I do for you). That didn’t seem like quite enough, though, until I thought about strawberries as a bridge: they are great with chocolate, they go well with cream cheese, and they pair beautifully with balsamic vinegar. Clearly what I needed to do was top the dessert with slices of strawberries, then boil down some of the balsamic into a syrup to drizzle over the fruit.

This was sounding further and further from the beautiful slice of tiramisu that we fought over in Ashland, which was served simply in a square portion with a little powdered sugar on the plate. The combination of cookie, custard, and fruit made me think of a trifle, and I determined I would serve these not as plated slices cut from a large cake, but in pretty cocktail glasses, with layers of each component to add visual appeal.

The result was terrifically rich, and while I’m not sure espresso, balsamic vinegar, and chocolate wafer cookies truly belong together, we did enjoy them. The real stand-out to the dessert, though, was the custard. At my first few spoonfuls, I was bowled over by a tartness I thought was the balsamic vinegar. The next day, though, when I allowed myself another serving, I realized the tanginess I was tasting came from the cream cheese. Mascarpone, the traditional thickener for the custard component, lacks this slight sourness (especially prominent in the Philadelphia brand); it is much more mild, almost like overwhipped cream just before it becomes butter. But the tangy flavor in the custard was reminiscent of cheesecake, which in my book is never a bad thing, and it kept the whole dessert from being overly sweet.

One note: you do have to watch the balsamic vinegar closely as it reduces, if you decide to go with the syrup option. In the space of about ten seconds, it goes from a lovely thick drizzle to an over-reduced sludge that hardens into a sticky caramel my fillings are still quivering about. Pull it off the heat a little before it seems reduced enough; it will continue to thicken as it cools.

These looked fantastic in my cocktail glasses, as you can see, but they were tremendously large and we ended up sharing just one to avoid overload. Smaller glasses, or even little jars, would be good for more, and less gluttonous, servings.

Tiramisu Trifles with Balsamic Drizzle

Makes 2 enormous or 4 small trifles, with custard left over

Minimum of about 3 hours, including chilling time (though chilling overnight is even better)

3 egg yolks

⅜ cups + 2 tablespoons sugar, divided

⅜ cups whole milk

4 ounces mascarpone cheese, at room temperature

6 ounces full fat cream cheese, at room temperature

½ cup boiling water

1 tablespoon espresso powder

½ cup + 2 tablespoons balsamic vinegar, divided

2 tablespoons rum, brandy, or marsala, optional

~ 12 chocolate wafer cookies, chopped or crumbled

4-6 fresh strawberries, sliced

Fill a large bowl about halfway with ice cubes and water. Use another small bowl and small pot to create a double boiler: bring a cup or two of water to a simmer in the pot, then set the small bowl atop it, being sure the bottom of the bowl does not touch the simmering water. Add the egg yolks and ⅜ cups of sugar to the bowl, then whisk until the sugar dissolves – you will no longer feel rough sugar granules against the whisk and the bowl.

Whisk in the ⅜ cups milk and then cook, whisking slowly and constantly, until the mixture reaches a temperature of 170F. This should take 10-15 minutes; look for the custard to become light and foamy, and thicken slightly.

Once the mixture hits its target temperature, remove the small bowl from the heat and place it gently into the larger bowl of ice water. Whisk for at least a minute until the mixture cools, taking care not to allow any ice water to slop into the custard.

In a medium bowl, use a spatula to firmly mix together the room temperature mascarpone and cream cheese. Then fold in the cooled custard just until fully incorporated and smooth. Top the bowl with plastic wrap and stow in the fridge until the other components are ready.

Now, add the espresso powder, 2 tablespoons balsamic vinegar, and the 2 tablespoons alcohol, if using, to the boiling water in a small pot or bowl. Stir to combine, then set aside to cool (I got impatient and shoved mine into the freezer for a few minutes).

When the espresso mixture has cooled, you are ready to assemble. First, soak the chopped or crumbled chocolate wafers in the espresso liquid for a few seconds. You want the liquid to permeate but you don’t want the cookie to sog into nothing. In cocktail glasses or dessert goblets, carefully add a layer of soaked cookie pieces. Top that with a layer of the cooled custard – it will still be fairly thin – then repeat: another layer of cookies, another layer of custard. You want at least two layers of each.

If it’s possible without disturbing the dessert layers, top each glass with plastic wrap and stow in the fridge again for at least 2 hours, but ideally longer – overnight is best.

About 20 minutes before you are ready for dessert, slice the strawberries. In a small pot, combine the remaining ½ cup of balsamic vinegar with the final 2 tablespoons sugar. Cook over medium heat, stirring occasionally, until the vinegar and sugar bubble down into a syrup; aim for the thickness of maple syrup, which will cool into something more like molasses. This will probably take anywhere from 5-10 minutes, depending on your stove and your pot.

Rescue your trifles from the fridge and for each, place a layer of strawberry slices in some artful design over the top. Drizzle on a few teaspoons of the balsamic syrup just before serving.